


Regrets?

by jessies_girl



Category: Supernatural
Genre: Bottom Dean, Daring Sam, First Time, M/M, Plot What Plot/Porn Without Plot, Smut, Top Sam, Wincest - Freeform
Language: English
Status: Completed
Published: 2016-09-09
Updated: 2016-09-09
Packaged: 2018-08-14 01:22:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,513
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7993432
Author URL: https://archiveofourown.org/users/jessies_girl/pseuds/jessies_girl
Summary: <blockquote class="userstuff">
              <p>After a hunt Sam wants to know if Dean has any regrets.</p>
            </blockquote>





	Regrets?

The hunt had been hard on both Dean and Sam. The wendigo had done a real number on them, exhausting the brothers enough to almost get the better of them. Dean had played bait, and a slip of his footing had put his life at risk as the wendigo was ready to shred him alive. Luckily Sam managed to shoot it with the flare gun before it's claws had ripped Dean's throat out.

Now they were sitting back in the motel, Dean, legs propped up on a chair and Sam staring out of the window, mind on God knew what.

"Are you getting morbid on me again?" Dean queried.

"No, I was just wondering. If you had died up there, what would you regret?" Sam looked squarely at his brother.

"Not much. I'm happy with what I've done with my life, the choices I've made." Dean looked up. "Most choices anyways."

"What about the choices you never got to make?" Sam's voice held a husky tinge. Dean frowned.

"I don't follow."

"There are things that I have dreamed of but never done. Maybe because I'm afraid, maybe because I've never been sure I wanted to pay the price. Then there are other things that I would really regret not doing," Sam elaborated.

"Like what?" Dean asked, knowing that it was a dangerous emotional question.

Sam leaned toward him, took the coffee mug from his brother's hand and placed it carefully on the table. Then he sat on the other bed, right opposite of Dean, their faces only inches apart.

"Sam?" Dean asked, as he started to feel a little trepidation. 

Sam's big hands landed on Dean's knees as he spread his legs. 

Dean gasped. "What are you doing?"

Sam didn't answer him, just slid his arms around Dean's waist, and cupped his ass, dragging him toward the edge. Dean squeaked in an embarrassingly girly way and drilled his eyes onto his brother's. 

Sam hands ran up Dean's back and cupped his shoulder blades. He slid off his bed, kneeling between his brother's spread legs and leaned in, putting their torsos against each other. The heat of their body spread through both of them and Dean grunted softly. His nipples hardened and he bit his lip to help keep his emotions under control. Sam always made Dean nervous when he got close. Not nervous nervous, but excited nervous. 

Then Sam's hands were cupping Dean's face and he stared straight into those green eyes. "At least once before I die, I want to know what it feels like to kiss these pouty, sexy lips of yours," he whispered.

"Sam! Geez! Where's this coming from?"

"I don't know. Maybe I'm just tired of regrets. Maybe I'm tired of worrying that one day all my chances will be gone." Sam smiled sadly.

"That's not going to happen," Dean said, voice sounding weak, even to himself.

"Neither of us can say." Sam leaned in and Dean couldn't find the energy to push him away. It wasn't that he didn't want to kiss his brother. In fact, that had been the subject of numerous daydreams since the day Sam had left for Stanford. If he let him know his true feelings, it could lead to an emotional disaster the size of a black hole. 

Dean took a deep breath and prepared to tell Sam they shouldn't do something just because they could. He never got the chance.

As soon as his mouth opened, Sam's lips covered Dean's in an open-mouthed kiss and his tongue darted out to brush over his top lip. The heat and moisture of Sam's raspy tongue sent tingles all through Dean's body, straight to his cock. A second later they were kissing passionately, like kissing each other was the only thing keeping them alive.

Dean realized very quickly that he was going to have no say in the matter. His brain had taken a vacation and his body was in charge. Every nerve ending seemed to come alive. 

Sam finally pulled back and said, "Let's feel alive, Dean. I have wanted to kiss you for so long, I just can't stand the thought of losing you without ever having loved you. Even at the risk of you hating me ever after." His soulful eyes connected with his brother's. Sometimes, no words were necessary.

"I could never hate you, Sammy," Dean rasped. "Especially as I'm feeling the very same."

Dean pulled Sam close, working his hands under his brothers tshirt. In no time he had pulled it over Sam's head, eyes admiringly roaming over his perfect torso. Dean softly ran his fingers over a scar on Sam's pecs, evoking a shiver from his younger brother. Getting bolder, Dean slipped his hand down over Sam's ass, pulling on his jeans. 

Getting the hint Sam stood up and rid himself of the remaining clothes and then let his fingers slip between Dean's legs, cupping his straining erection through the denim.

"You're way overdressed, Dean," Sam purred, tugging on Dean's belt. With a keening growl, Dean pulled off his shirt and made short work of his shoes, socks and jeans. Clad only in his boxers, which were pitching a tent you could see from miles away, he smirked at his brother.

Sam moaned and grabbed the waistband, roughly tugging them down to reveal the beautifully leaking cock. He brushed his fingertips lightly over his brother's trembling thigh, grinning when Dean bit his sinful bottom lip to stifle a moan.

He pushed Dean back on the bed and descended upon him, kissing him deeply. His painfully erect cock rolled up and over his balls, then lined up alongside his brother's. Keeping a lazy pace Sam created enough friction between the two to make him buck his hips.

Then Sam leaned down to suckle an invitingly hard nipple and Dean moaned, letting his hands roam across Sam's backside until he found his ass cheeks, giving them a squeeze. 

"Oh God, I've always loved your ass," Dean groaned and in response Sam gently bit down on Dean's spit wet nipple. Sam dredged up yet another groan as he fit his hand between them and stroked Dean's length from hilt to tip, spreading the precum over the sensitive head.

Dean was so hard it felt like he would snap. He couldn't believe how hot he'd gotten so quickly.

"Sam, please. I promise I'll do all the fun stuff another time, but right now, I really need you to be inside me."

"Fuck, Dean, yes," Sam hissed, using his long, precum slick fingers to work open his brother's puckered hole. Looking up into Dean lust blown eyes took away the last hint of a doubt Sam had. He lined his cock up against his brother and slowly pressed into the tight entrance.

Dean sucked in the air briefly, at the sensation of being filled up by his baby brother. He had never thought Sam would want him that way, so he had never asked, but it was so obvious now, Sam in full arousal mode because of him. Dean's heart was beating rapidly in his chest and he felt himself relax as Sam's hot cock slid in deeper.

Sam's breathing was hitching, the feeling of being inside Dean, feeling how tight he was, feeling his heat engulf him, was such a delicious one that he feared he wouldn't be able to hold very long. Finally he felt his balls slap against Dean's ass. Sam looked at his brother again, their eyes locking. Then Dean squeezed Sam's sheathed cock and Sam groaned loudly.

"What are you waiting for, Sammy," Dean rasped. "Need you so bad."

And Sam didn't need any further encouragement. He pulled back and then snapped his hips forward, picking up speed on the way.

"So good, baby brother," Dean mumbled, eyes closing in bliss as he felt the tip of his brother's cock brush over his prostate, again and again. Sam's moaning became erratic, his balls were tingling and his whole body felt like it was about to explode.

"Dean," Sam said, body trembling, "I'm..."

"It's okay, Sammy," Dean ran his hand over his brother's biceps. "Just go with the flow."

Dean's own cock was painfully hart, drooling precum like Sammy opened a tap. He knew feeling his brother come undone inside of him would send him over the edge and as much as he enjoyed prolongued sex right now all he wanted to do is blow his load.

Sam kept his pace, his right hand straying towards his brother's cock without breaking his rhythm. The second he touched the overexcited precum slick head, Dean shouted in pleasure and bucked up, squeezing down on Sam's cock in reflex. Sam felt Dean's hot cum hit his tense abs and with a final snap of his hips buried himself as deep as could go, shooting his own load deep inside Dean. 

"Fuck, Sam... you're an animal," Dean slurred as he felt his brother slip out. Sam grinned, sated, spooning up behind his brother and nuzzled Dean's ear with his lips.

"And you are hot."

**Author's Note:**

> Just a small piece that jumped me... not really a bottom Dean person but it seemed right here.
> 
> Written for my hat girlz Jess, Teresa and Jennie. I know Jessie likes bottom Dean.


End file.
